Daniel Squadron, The Mouthy Candidate Who Won’t Talk

September 3, 2008

Daniel Squadron, a wealthy first-time political candidate, is running a smart and aggressive campaign against one of Albany’s most veteran incumbents. The 28-year-old Yale graduate is giving State Senator Marty Connor, who won office before Squadron was born, a tough race for his money. Unfortunately, the would-be pol is also proving to have a glass jaw: He can dish it out, but he can’t take it.

Since announcing his campaign early this year to win the Democratic nomination for the senate seat representing lower Manhattan and a slice of north Brooklyn, Squadron has waged a steady series of slash-and-burn attacks on his opponent.

Much of it is fair game. Squadron has slammed Connor for using his skills as a top election lawyer for non-Democrats and for knocking challengers off the ballot. Point scored. He’s lanced him as well for taking contributions from landlords and Albany’s business-as-usual crowd. Two points. He also came up with a snotty—but perfectly legitimate—way to tell voters about an old tax lien the feds filed against Connor a few years ago: On April 15, Squadron—who trained under U.S. Senator Chuck Schumer—issued a press release reminding Connor to file his taxes. Ouch. Connor, then in session in Albany, squirmed and had to quickly re-explain (a prior opponent had also cited the lien) that he’d made an error in figuring his alternative minimum tax, followed by a losing battle with the IRS about how much he owed. Squadron’s team snorted to reporters: You’re not buying that one, are you?

The challenger has also launched a slew of other blasts at Connor’s record, some of them sloppily wide of the mark, others that are just outright distortions. But, hey, it’s politics. Connor has been at this a long time and should be able to take it. If his constituents don’t know his real record, whose fault is that?

But as soon as questions are thrown at the brawling challenger, the whining starts. Asked last week why he hadn’t disclosed the details of his sizable trust-fund holdings on his state financial-disclosure report, Squadron refused to even comment. “I am not going to be able to talk to you on the record,” he said. Squadron’s spokesman weighed in this way in an e-mail: “For the record, I have to say I am disturbed by your approach to this race,” wrote aide Josh Kriegman. “You seem to remain engaged exclusively in a one-sided fishing expedition.”

Actually, little fishing was required. If it wasn’t for the ample personal wealth he brings to the table, Squadron’s campaign wouldn’t be any more noteworthy than any other rookie swinging for the fences against a longtime incumbent. But Squadron’s got his own money and access to more: So far he’s raised half a million dollars for the race, much of it from affluent family friends and supporters of his key patron, Schumer.

Squadron is the son of a top attorney whose clients included Rupert Murdoch. The 2007 tax returns he shared with reporters (Connor released the last five years; Squadron said one was enough) show that he earned $200,000 in dividends and capital gains from a trust fund held in his mother’s name. State laws mandate that candidates and office holders answer questions about their holdings so that the public can get some notion of personal interest or bias.

These questions are always stickiest for those who have real dough. On the question about stock holdings, Squadron skated, providing only the name of the brokerage firm holding the trust fund. State instructions on answering this question seem pretty clear: “You also need to list securities held for your benefit by a brokerage firm or nominee.” Asked if there was some kind of wiggle room here, a state official said: “Obviously, we stand by what we say.”

Squadron won’t talk about any of this for the record. Suffice it to say that well-informed campaign sources said that “experts” had advised him that he didn’t have to list the holdings. OK, fair enough. But since Squadron’s entire platform is devoted to bringing transparency and reform to the legislature, what’s the big deal about disclosing them? No comment.

The challenger’s upstart bid got even more credible last month when he won twin endorsements from The New York Times and Mayor Bloomberg. The Times lambasted Connor for having “accomplished far too little” in his years in office; it praised Squadron as “an enthusiastic newcomer” who is “committed to cleaning up Albany.” The editorial also added a gentle reproach: “If Mr. Squadron wants to prove his commitment to reform,” the editheads wrote, “then he still needs to be more forthcoming about his financial holdings.”

Funny thing—a glossy mailer sent to voters by Squadron proclaiming the Times endorsement excised that sentence with four little dots.

And it’s not just discussion of his money that he wants to skip over. In his endorsement, Bloomberg called Squadron “exactly what New York City needs in our state capitol.” But the two men are not exactly on the same page on this score. The mayor is not only the strongest political ally of the Republican majority in the senate, he’s also their biggest single campaign contributor. In February, Bloomberg donated $500,000 to the senate Republicans. Some of that money is being spent right now on TV ads boosting the endangered candidacy of Serf Maltese, the conservative Queens Republican who is battling a tough Democratic challenge.

Squadron insists that he wants to be part of a new Democratic majority in the senate that will bring reforms and progressive legislation. So how does he square taking an endorsement from the senate GOP’s biggest backer? No comment. A source familiar with the candidate’s thinking said he would disagree with Bloomberg—if asked about it.

Then there’s Squadron’s own exceedingly thin record. In his blustering endorsement, Bloomberg proclaimed that Squadron’s “record [of] getting things done for New Yorkers is already more impressive than many lifelong legislators.” Hmmm. Aside from a brief stint as a paid consultant to the Department of Education, running a bar on the Upper West Side with friends, and helping Schumer write a book, Squadron’s entire five-year-long career has been politics.

In addition to Schumer, he’s worked for Anthony Weiner and Andrew Cuomo. Last year, he was a hired gun working on campaigns for Knickerbocker SKD, the fast-growing consulting firm founded by ex-Schumer aide Josh Isay (whose clients include Bloomberg and other politicians who have endorsed Squadron).

There was also a few weeks’ work in 2005 as communications director on the campaign to pass the state transportation bond. Squadron touts this mini-job as evidence that he can bring resources to the city. Actually, while the bond act was endorsed by good-government groups, its promotion was paid for by the contractors and building trades who stood to benefit from it, and handled by the state’s biggest lobbying firms. Asked how he got that job, Squadron declined comment.

Don’t try pressing Bloomberg, though, on Squadron’s specific achievements. A couple days after his endorsement, recorded the Daily News‘ Liz Benjamin, the mayor couldn’t quite recall the name. “The new young guy, uh, Brian Sargeant, um, really is somebody dynamic.”